NPASS drugs

Drug Information

Drug ID:	NPD5157
Drug Name:	Lobeline
Molecular Formula:	C22H27NO2
Canonical SMILES:	O[C@H](c1ccccc1)C[C@@H]1CCC[C@@H](N1C)CC(=O)c1ccccc1
Standard InCHI:	InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
Standard InCHIKey:	MXYUKLILVYORSK-HBMCJLEFSA-N
Max Developmental Stage:	Phase 1
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5157

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	91
0.1-0.2	532
0.2-0.3	1804
0.3-0.4	5539
0.4-0.5	9281
0.5-0.6	10914
0.6-0.7	2634
0.7-0.8	88
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC285394
High Similarity	0.8707	NPC65855
High Similarity	0.8707	NPC292758
Intermediate Similarity	0.8362	NPC167336
Intermediate Similarity	0.8359	NPC305717
Intermediate Similarity	0.814	NPC65310
Intermediate Similarity	0.811	NPC26285
Intermediate Similarity	0.7966	NPC249067
Intermediate Similarity	0.791	NPC313663
Intermediate Similarity	0.7829	NPC84281
Intermediate Similarity	0.7829	NPC291027
Intermediate Similarity	0.7829	NPC317474
Intermediate Similarity	0.7829	NPC213126
Intermediate Similarity	0.7829	NPC169485
Intermediate Similarity	0.781	NPC281104
Intermediate Similarity	0.7759	NPC289201
Intermediate Similarity	0.7724	NPC68967
Intermediate Similarity	0.7664	NPC474787
Intermediate Similarity	0.7664	NPC79465
Intermediate Similarity	0.7664	NPC76785
Intermediate Similarity	0.7664	NPC474855
Intermediate Similarity	0.7664	NPC9687
Intermediate Similarity	0.7664	NPC475318
Intermediate Similarity	0.7664	NPC474811
Intermediate Similarity	0.7664	NPC90194
Intermediate Similarity	0.7664	NPC476102
Intermediate Similarity	0.7664	NPC293377
Intermediate Similarity	0.7664	NPC118099
Intermediate Similarity	0.7664	NPC273907
Intermediate Similarity	0.7664	NPC151706
Intermediate Similarity	0.7664	NPC260045
Intermediate Similarity	0.7664	NPC475598
Intermediate Similarity	0.7664	NPC49577
Intermediate Similarity	0.7576	NPC307020
Intermediate Similarity	0.7563	NPC214200
Intermediate Similarity	0.7563	NPC228400
Intermediate Similarity	0.7519	NPC474847
Intermediate Similarity	0.748	NPC211439
Intermediate Similarity	0.7445	NPC257390
Intermediate Similarity	0.7426	NPC69496
Intermediate Similarity	0.741	NPC473360
Intermediate Similarity	0.7402	NPC196673
Intermediate Similarity	0.7385	NPC249435
Intermediate Similarity	0.7361	NPC297322
Intermediate Similarity	0.7353	NPC103605
Intermediate Similarity	0.7353	NPC81092
Intermediate Similarity	0.7353	NPC469666
Intermediate Similarity	0.7348	NPC472981
Intermediate Similarity	0.7338	NPC474473
Intermediate Similarity	0.7305	NPC316906
Intermediate Similarity	0.7288	NPC206764
Intermediate Similarity	0.7266	NPC233910
Intermediate Similarity	0.7266	NPC245836
Intermediate Similarity	0.7254	NPC153007
Intermediate Similarity	0.7244	NPC158282
Intermediate Similarity	0.7222	NPC158854
Intermediate Similarity	0.7213	NPC25458
Intermediate Similarity	0.7209	NPC285350
Intermediate Similarity	0.7177	NPC105899
Intermediate Similarity	0.7177	NPC211551
Intermediate Similarity	0.7165	NPC476003
Intermediate Similarity	0.7154	NPC23402
Intermediate Similarity	0.7154	NPC255676
Intermediate Similarity	0.7132	NPC4974
Intermediate Similarity	0.7132	NPC477249
Intermediate Similarity	0.7132	NPC477248
Intermediate Similarity	0.7122	NPC120251
Intermediate Similarity	0.7109	NPC471188
Intermediate Similarity	0.7107	NPC329387
Intermediate Similarity	0.7107	NPC317280
Intermediate Similarity	0.7101	NPC116057
Intermediate Similarity	0.7097	NPC226778
Intermediate Similarity	0.7097	NPC304761
Intermediate Similarity	0.7097	NPC147000
Intermediate Similarity	0.7097	NPC150254
Intermediate Similarity	0.7083	NPC150712
Intermediate Similarity	0.7063	NPC141523
Intermediate Similarity	0.7049	NPC217621
Intermediate Similarity	0.7034	NPC141607
Intermediate Similarity	0.7034	NPC187725
Intermediate Similarity	0.7032	NPC476750
Intermediate Similarity	0.7031	NPC116842
Intermediate Similarity	0.7031	NPC252544
Intermediate Similarity	0.7031	NPC321252
Intermediate Similarity	0.7031	NPC474057
Intermediate Similarity	0.7025	NPC476749
Intermediate Similarity	0.7023	NPC188010
Intermediate Similarity	0.7023	NPC322197
Intermediate Similarity	0.7021	NPC328070
Intermediate Similarity	0.7016	NPC329556
Intermediate Similarity	0.7015	NPC190663
Intermediate Similarity	0.7014	NPC471316
Intermediate Similarity	0.7013	NPC476443
Intermediate Similarity	0.7013	NPC133817
Intermediate Similarity	0.7007	NPC47667
Remote Similarity	0.6984	NPC95178
Remote Similarity	0.6984	NPC29989
Remote Similarity	0.6984	NPC69332
Remote Similarity	0.698	NPC476444
Remote Similarity	0.6978	NPC472413
Remote Similarity	0.6977	NPC66208
Remote Similarity	0.6977	NPC177576
Remote Similarity	0.6972	NPC266425
Remote Similarity	0.6967	NPC108606
Remote Similarity	0.6967	NPC164514
Remote Similarity	0.6967	NPC303611
Remote Similarity	0.6967	NPC290515
Remote Similarity	0.6967	NPC229242
Remote Similarity	0.6967	NPC226096
Remote Similarity	0.6957	NPC275576
Remote Similarity	0.6954	NPC469539
Remote Similarity	0.6954	NPC469540
Remote Similarity	0.6953	NPC88141
Remote Similarity	0.6953	NPC95172
Remote Similarity	0.6944	NPC473052
Remote Similarity	0.6944	NPC473055
Remote Similarity	0.694	NPC473767
Remote Similarity	0.694	NPC472708
Remote Similarity	0.6935	NPC304873
Remote Similarity	0.6935	NPC327226
Remote Similarity	0.6923	NPC128368
Remote Similarity	0.6923	NPC272524
Remote Similarity	0.6918	NPC251439
Remote Similarity	0.6913	NPC246412
Remote Similarity	0.6912	NPC160493
Remote Similarity	0.6906	NPC199738
Remote Similarity	0.6906	NPC169913
Remote Similarity	0.6906	NPC210950
Remote Similarity	0.6905	NPC473418
Remote Similarity	0.6899	NPC265513
Remote Similarity	0.6897	NPC322526
Remote Similarity	0.6897	NPC471201
Remote Similarity	0.6889	NPC27833
Remote Similarity	0.6887	NPC144691
Remote Similarity	0.6885	NPC253423
Remote Similarity	0.6884	NPC295664
Remote Similarity	0.688	NPC474365
Remote Similarity	0.688	NPC301943
Remote Similarity	0.6879	NPC262819
Remote Similarity	0.6879	NPC204867
Remote Similarity	0.6875	NPC469636
Remote Similarity	0.6875	NPC17525
Remote Similarity	0.6875	NPC318327
Remote Similarity	0.6875	NPC317305
Remote Similarity	0.6875	NPC208725
Remote Similarity	0.687	NPC474363
Remote Similarity	0.6866	NPC318173
Remote Similarity	0.6861	NPC223351
Remote Similarity	0.6855	NPC316797
Remote Similarity	0.6855	NPC42211
Remote Similarity	0.685	NPC45033
Remote Similarity	0.685	NPC70843
Remote Similarity	0.6846	NPC114682
Remote Similarity	0.6846	NPC212718
Remote Similarity	0.6842	NPC158157
Remote Similarity	0.6829	NPC175852
Remote Similarity	0.6829	NPC160548
Remote Similarity	0.6829	NPC210529
Remote Similarity	0.6825	NPC8931
Remote Similarity	0.6825	NPC261573
Remote Similarity	0.6825	NPC120693
Remote Similarity	0.6824	NPC908
Remote Similarity	0.6824	NPC138438
Remote Similarity	0.6818	NPC474095
Remote Similarity	0.6818	NPC306740
Remote Similarity	0.6818	NPC186933
Remote Similarity	0.6812	NPC85511
Remote Similarity	0.6807	NPC62765
Remote Similarity	0.6797	NPC249811
Remote Similarity	0.6797	NPC34715
Remote Similarity	0.6797	NPC226699
Remote Similarity	0.6794	NPC470253
Remote Similarity	0.6788	NPC167323
Remote Similarity	0.6788	NPC269923
Remote Similarity	0.6786	NPC218323
Remote Similarity	0.6783	NPC475042
Remote Similarity	0.6777	NPC34243
Remote Similarity	0.6777	NPC261181
Remote Similarity	0.6774	NPC118343
Remote Similarity	0.6772	NPC134120
Remote Similarity	0.6772	NPC269457
Remote Similarity	0.6769	NPC21162
Remote Similarity	0.6769	NPC210089
Remote Similarity	0.6767	NPC471616
Remote Similarity	0.6765	NPC80150
Remote Similarity	0.6761	NPC183722
Remote Similarity	0.6759	NPC109580
Remote Similarity	0.675	NPC35345
Remote Similarity	0.6748	NPC471743
Remote Similarity	0.6746	NPC160382
Remote Similarity	0.6744	NPC475282
Remote Similarity	0.6744	NPC224584
Remote Similarity	0.6742	NPC242136
Remote Similarity	0.6742	NPC11824
Remote Similarity	0.6742	NPC153053
Remote Similarity	0.6741	NPC184527
Remote Similarity	0.6741	NPC41567
Remote Similarity	0.6739	NPC86900
Remote Similarity	0.6739	NPC35996
Remote Similarity	0.6738	NPC17374

Drug Structure

NPD5157 OpenBabel08211706322D 26 28 0 0 1 0 0 0 0 0999 V2000 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 15 1 1 0 0 0 19 23 1 0 0 0 0 20 16 1 1 0 0 0 20 23 1 0 0 0 0 21 15 1 6 0 0 0 21 24 1 0 0 0 0 22 25 2 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB05137
ChEMBL	CHEMBL122270
IUPHAR/BPS
PharmaGKB
KEGG Drug	D02364
PubChem CID
ChEBI	48723
CAS Number	90-69-7

Drug Properties

Molecular Weight	337.20
ALogP	-1.877
MLogP	3.55
XLogP	6.146
HDA	3
HBD	1
Rotatable Bonds	8
TPSA	40.54
RO5 Violation	1